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Cheap flights from New York to Chicago from $181

NYC — CHI
7 Nov — 14 Nov1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 83 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago

Tue 27/1019:35 -
Nonstop3h 08m
Thu 29/1006:10 -
Nonstop2h 17m
Deal found 8/10$353
Sat 7/1114:00 -
Nonstop2h 30m
Mon 9/1105:00 -
Nonstop2h 05m
Deal found 8/10$353
Wed 11/1106:40 -
1 stop6h 20m
Tue 17/1113:00 -
1 stop7h 29m
Deal found 7/10$355
Mon 26/1020:35 -
Nonstop2h 42m
Thu 29/1006:00 -
Nonstop2h 12m
Deal found 8/10$355
Thu 19/1110:00 -
Nonstop2h 40m
Mon 23/1105:00 -
Nonstop2h 05m
Deal found 4/10$355
Wed 11/1106:40 -
1 stop6h 20m
Sat 14/1113:00 -
1 stop7h 29m
Deal found 5/10$356
Mon 26/1020:25 -
Nonstop2h 51m
Thu 29/1008:00 -
Nonstop2h 12m
Deal found 7/10$356
Thu 29/1006:40 -
1 stop6h 20m
Wed 4/1113:00 -
1 stop7h 29m
Deal found 6/10$357
Fri 6/1116:25 -
1 stop7h 20m
Tue 10/1108:10 -
2 stops7h 45m
Deal found 5/10$357
Fri 13/1113:26 -
1 stop6h 51m
Sat 14/1113:00 -
1 stop7h 29m
Deal found 6/10$359
Wed 28/1014:40 -
Nonstop2h 46m
Thu 29/1006:00 -
Nonstop2h 12m
Deal found 7/10$359
Fri 6/1116:25 -
1 stop7h 20m
Mon 9/1108:45 -
1 stop8h 10m
Deal found 5/10$359

Find flight deals from New York to Chicago

Round-trip from

$353

One-way from

$181

Popular in

July

Cheapest in

January

Average price

$444

Good one-way deal

$219 or less
Delta
  • Delta
  • 27/10-29/10
  • Nonstop
  • 5h 25m total
  • New York to Chicago
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JetBlue
  • JetBlue
  • 11/12-31/12
  • 1 total stop
  • 5h 07m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($94 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average return price).
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Average for round-trip flights in October 2026
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Price to beat on a one-way flight from New York (NYC) to Chicago (CHI).
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Tue 3/11

14:34-16:21

Nonstop2h 47m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$211

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 12/11

13:29-15:13

Nonstop2h 44m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$212

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Tue 16/2

18:05-19:57

Nonstop2h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$212

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sun 22/11

08:00-09:45

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$214

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Fri 25/12

07:07-09:00

Nonstop2h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$214

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 21/12

06:00-07:52

Nonstop2h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$218

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Thu 29/10

06:40-12:00

1 stop6h 20m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$221

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Wed 4/11

19:35-21:43

Nonstop3h 08m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$221

New YorkChicago

LGA New York LaGuardia - MDW Chicago Midway

LGAMDW

New York LaGuardia

Fri 6/11

06:45-08:10

Nonstop2h 25m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

$221

New YorkChicago

JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl

JFKORD

New York John F Kennedy Intl

Thu 1/4

07:30-09:24

Nonstop2h 54m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$221

Flights are sorted by cheapest return flights first.

Deals found on 8/10

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

What is the cheapest month to book a flight from New York to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $274). Flying from New York to Chicago in July is currently the most expensive (average of $495). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 86% versus a flight in the afternoon.

Weekly flight availability from New York to Chicago

The most flights from NYC to CHI are scheduled on a Wednesday (184 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (89 on average).

How much does it cost for a return flight from New York to Chicago?

Airfare is typical for this route at the moment.
New York to Chicago flights typically cost between $316 and $573 in October.
The cheapest return price found within the last 5 days was $353 on Delta (27 Oct–29 Oct).

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

How far ahead should I book a flight from New York to Chicago?

The best time to book flights from New York to Chicago is 82 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

  • How long is the flight from New York to Chicago?

    Airlines like Delta, Southwest, and United Airlines fly from New York to Chicago in about 2h 20m. The time it takes to get you to your destination is usually consistent. New York and Chicago are separated by a distance of 1162 km. Generally, flights for this route are direct.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Malaysia Airlines (76%), American Airlines (75%), Air Europa (75%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $274). Flying from New York to Chicago in July is currently the most expensive (average of $495). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for New York to Chicago

Newark to O'Hare Intl flights

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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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